US20210060907A1 - Intermediate film for laminated glass and laminated glass - Google Patents

Intermediate film for laminated glass and laminated glass Download PDF

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Publication number
US20210060907A1
US20210060907A1 US16/965,200 US201916965200A US2021060907A1 US 20210060907 A1 US20210060907 A1 US 20210060907A1 US 201916965200 A US201916965200 A US 201916965200A US 2021060907 A1 US2021060907 A1 US 2021060907A1
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US
United States
Prior art keywords
layer
interlayer film
cured product
resin
laminated glass
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Abandoned
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US16/965,200
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English (en)
Inventor
Yuki Ishikawa
Shinji Kawada
Tatsuya Iwamoto
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sekisui Chemical Co Ltd
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Sekisui Chemical Co Ltd
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Publication date
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Assigned to SEKISUI CHEMICAL CO., LTD. reassignment SEKISUI CHEMICAL CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: IWAMOTO, TATSUYA, ISHIKAWA, YUKI, KAWADA, SHINJI
Publication of US20210060907A1 publication Critical patent/US20210060907A1/en
Abandoned legal-status Critical Current

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Definitions

  • the present invention relates to an interlayer film for laminated glass which is used for obtaining laminated glass. Moreover, the present invention relates to a laminated glass prepared with the interlayer film for laminated glass.
  • laminated glass Since laminated glass generates only a small amount of scattering glass fragments even when subjected to external impact and broken, laminated glass is excellent in safety. As such, the laminated glass is widely used for automobiles, railway vehicles, aircraft, ships, buildings and the like.
  • the laminated glass is produced by sandwiching an interlayer film for laminated glass between two glass plates.
  • Patent Document 1 discloses an interlayer film having a sound insulating layer formed of composition (A) containing at least one resin (al) selected from a thermoplastic resin and a thermosetting resin.
  • Tan ⁇ that is obtained when the dynamic viscoelasticity of the sheet formed of the aforementioned composition to have a thickness of 0.8 mm is measured at a frequency of 0.3 Hz in a tensile mode has the maximum value at temperature T A (° C.).
  • T A (° C.) ranges from ⁇ 50 to 50° C.
  • tan ⁇ at T A (° C.) is 2.5 or more.
  • Patent Document 1 indicates polyvinyl acetal, polyvinyl alcohol, polyurethane, polyvinyl carboxylate, olefin-vinyl carbonate copolymer, polyurethane elastomer, polyester elastomer, styrene-diene block copolymer, and chlorinated polyolefin, as the thermoplastic resin.
  • Patent Document 1 indicates epoxy resins, phenol resins, urethane resins, melamine resins, and unsaturated polyester resins as the thermosetting resin.
  • Patent Document 1 indicates that the sound insulating property of the interlayer film is enhanced.
  • the temperature at which the mean value of the sound transmission loss is the largest are indicated.
  • Patent Document 2 discloses a photocurable resin composition for an interlayer film for laminated glass.
  • the photocurable resin composition contains a (meth)acrylic polymer, a methacrylic monomer, and a photopolymerization initiator.
  • Patent Document 2 indicates that a laminated glass that is difficult to be broken when an impact is applied from outside can be obtained.
  • Patent Document 1 WO2017/170259A1
  • Patent Document 2 WO2017/209013A1
  • a laminated glass including an interlayer film is used in various temperature environments. In a laminated glass prepared with a conventional interlayer film, it is sometimes the case that the sound insulating property cannot be enhanced over a wide range of temperature.
  • a laminated glass having high sound insulating property at a specific one temperature can have low sound insulating property when the laminated glass is used at a temperature different from the specific one temperature.
  • Patent Document 1 indicates that the sound insulating property of the interlayer film is enhanced. While Patent Document 1 evaluates the sound transmission loss at temperatures of 0° C., 5° C., 10° C., 15° C., 20° C., 25° C., 30° C., 35° C. and 40° C., it lacks description of results of sound transmission loss at every temperature of the plurality of temperatures. Patent Document 1 fails to indicate enhancement of the sound insulating property over a wide range of temperature by Examples.
  • Patent Document 2 indicates that a laminated glass that is difficult to be broken when an impact is applied from outside can be obtained, it lacks the description about the sound insulating property in the photocurable resin composition.
  • the present invention is aimed at providing an interlayer film for laminated glass capable of enhancing the sound insulating property over a wide range of temperature from 10° C. to 30° C. Moreover, the present invention is also aimed at providing laminated glass prepared with the interlayer film for laminated glass.
  • an interlayer film for laminated glass having a one-layer structure or a two or more-layer structure
  • the interlayer film including a layer containing a cured product, the cured product being a cured product of a photocurable compound or a moisture-curable compound, or a cured product of a curable compound having a (meth)acryloyl group, the layer containing a cured product having a peak temperature of tan ⁇ of ⁇ 50° C. or more and 30° C. or less and having tan ⁇ at the peak temperature of tan ⁇ of 2.0 or more in viscoelasticity measurement at a frequency of 1 Hz and in a shearing mode.
  • the cured product is a cured product of a photocurable compound.
  • the layer containing a cured product has a storage modulus G′ at 100° C. of 5.0 ⁇ 10 3 Pa or more.
  • a peak temperature of tan ⁇ is ⁇ 30° C. or more and 20° C. or less in viscoelasticity measurement at a frequency of 1 Hz and in a shearing mode for the layer containing a cured product.
  • the interlayer film is an interlayer film for laminated glass having a two or more-layer structure, and the interlayer film includes a layer containing a resin that is different from the cured product.
  • the interlayer film for laminated glass has a two or more-layer structure
  • the interlayer film includes a layer containing a resin that is different from the cured product, and in viscoelasticity measurement at a frequency of 1 Hz and in a shearing mode for the interlayer film, a peak temperature of tan ⁇ of the layer containing a resin that is different from the cured product is ⁇ 100° C. or more and 100° C.
  • a ratio of tan ⁇ at a peak temperature of tan ⁇ of the layer containing a cured product, to tan ⁇ at a peak temperature of tan ⁇ of the layer containing a resin that is different from the cured product in viscoelasticity measurement at a frequency of 1 Hz and in a shearing mode for the interlayer film is 2.0 or more and 10.0 or less.
  • a laminated glass including a first lamination glass member, a second lamination glass member, and the above-described interlayer film for laminated glass, the interlayer film for laminated glass being arranged between the first lamination glass member and the second lamination glass member.
  • the interlayer film for laminated glass according to the present invention has a one-layer structure or a two or more-layer structure.
  • the interlayer film for laminated glass according to the present invention includes a layer containing a cured product.
  • the cured product is a cured product of a photocurable compound or a moisture-curable compound, or a cured product of a curable compound having a (meth)acryloyl group.
  • a peak temperature of tan ⁇ is ⁇ 50° C. or more and 30° C.
  • tan ⁇ at the peak temperature of tan ⁇ is 2.0 or more in viscoelasticity measurement at a frequency of 1 Hz and in a shearing mode for the cured product.
  • tan ⁇ at the peak temperature of tan ⁇ is 2.0 or more in viscoelasticity measurement at a frequency of 1 Hz and in a shearing mode for the cured product.
  • FIG. 1 is a sectional view schematically showing an interlayer film for laminated glass in accordance with a first embodiment of the present invention.
  • FIG. 2 is a sectional view schematically showing an interlayer film for laminated glass in accordance with a second embodiment of the present invention.
  • FIG. 3 is a sectional view schematically showing an example of laminated glass prepared with the interlayer film for laminated glass shown in FIG. 1 .
  • FIG. 4 is a sectional view schematically showing an example of laminated glass prepared with the interlayer film for laminated glass shown in FIG. 2 .
  • the interlayer film for laminated glass according to the present invention (hereinafter, sometimes described as interlayer film) has a one-layer structure or a two or more-layer structure.
  • the interlayer film according to the present invention includes a layer containing a cured product.
  • the cured product is a cured product of a photocurable compound or a moisture-curable compound, or a cured product of a curable compound having a (meth)acryloyl group.
  • the curable compound may be a photocurable compound or a moisture-curable compound, or may be a curable compound having a (meth)acryloyl group.
  • the curable compound having a (meth)acryloyl group may be a photocurable compound or may be a moisture-curable compound, or may be a curable compound that is different from both the photocurable compound and the moisture-curable compound.
  • the compound cures by irradiation with light.
  • the cured product contained in the layer containing a cured product is generally a resin. Therefore, the layer containing a cured product is also referred to as a first resin layer.
  • a peak temperature of tan ⁇ is ⁇ 50° C. or more and 30° C. or less, and tan ⁇ (1) at the peak temperature of tan ⁇ is 2.0 or more in viscoelasticity measurement at a frequency of 1 Hz and in a shearing mode for the layer containing a cured product.
  • the interlayer film according to the present invention since the aforementioned configuration is provided, it is possible to enhance the sound insulating property over a wide range of temperature including 10° C. to 30° C. For example, it is possible to enhance the sound insulating property not at only one of temperatures selected, for example, from 10° C., 20° C., and 30° C., but at all these three temperatures. Therefore, in the interlayer film according to the present invention, it is possible to exert high sound insulating property even when a laminated glass prepared with the interlayer film is used in various temperature environments.
  • the interlayer film according to the present invention since migration of the plasticizer and other additive is small, and the compatibility is excellent even if these ingredients migrate, the transparency is difficult to deteriorate by storage, and the haze is difficult to change even if the interlayer film is stored.
  • the peak temperature of tan ⁇ of the layer containing a cured product is preferably ⁇ 45° C. or more, more preferably ⁇ 40° C. or more, still more preferably ⁇ 35° C. or more, further preferably ⁇ 30° C. or more, still further preferably ⁇ 25° C. or more, especially preferably ⁇ 20° C. or more, and most preferably ⁇ 10° C. or more.
  • the peak temperature of tan ⁇ of the layer containing a cured product is preferably 25° C. or less, more preferably 20° C. or less, further preferably 15° C. or less, and especially preferably 10° C. or less.
  • tan ⁇ (1) at the peak temperature of tan ⁇ of the layer containing a cured product is preferably 2.2 or more, more preferably 2.4 or more, still more preferably 2.5 or more, especially preferably 2.6 or more, further preferably 2.8 or more, and still further preferably 3.0 or more.
  • the upper limit of tan ⁇ (1) at the peak temperature of tan ⁇ is not limited.
  • the tan (1) at the peak temperature of tan ⁇ may be 6 or less.
  • the storage modulus G′ at 100° C. of the layer containing a cured product is preferably 5.0 ⁇ 10 3 Pa or more, more preferably 1.0 ⁇ 10 4 Pa or more, still more preferably 2.0 ⁇ 10 4 Pa or more, further preferably 3.0 ⁇ 10 4 Pa or more, still further preferably 4.0 ⁇ 10 4 Pa or more, and especially preferably 5.0 ⁇ 10 4 Pa or more
  • the storage modulus G′ at 100° C. of the layer containing a cured product is the above lower limit or more, the sound insulating property is further enhanced over a wide range of temperature. Also, when the storage modulus G′ at 100° C.
  • the sound insulating property in the high frequency region of 5000 Hz to 10000 Hz is further enhanced, and the road noise in an automobile or the like in which the interlayer film is used is reduced.
  • the curable compound is preferably a photocurable compound, and preferably a curable compound having a (meth)acryloyl group.
  • the cured product is preferably a (meth)acrylic polymer.
  • the interlayer film include a layer containing a resin that is different from the cured product. It is preferred that the resin contained in the layer containing a resin be a cured product of a thermosetting compound or a thermoplastic resin. When the resin is a cured product of a curable compound, it is preferred that the curable compound be a thermosetting compound.
  • the layer containing a resin that is different from the cured product is also referred to as a second resin layer.
  • the peak temperature of tan ⁇ in viscoelasticity measurement at a frequency of 1 Hz and in a shearing mode for the layer containing a resin (second resin layer) is preferably ⁇ 100° C. or more, and is preferably 100° C. or less.
  • the peak temperature of tan ⁇ of the layer containing a resin is preferably ⁇ 90° C. or more, and more preferably ⁇ 80° C. or more, and is preferably 90° C. or less, and more preferably 80° C. or less.
  • Viscoelasticity measurement is conducted for an interlayer film having a two or more-layer structure including a layer containing a resin that is different from a cured product.
  • a ratio of tan ⁇ (1) at the peak temperature of tan ⁇ of the layer containing a cured product (first resin layer) to tan ⁇ (2) at the peak temperature of tan ⁇ of the layer containing a resin that is different from the cured product (second resin layer) in viscoelasticity measurement at a frequency of 1 Hz in a shearing mode for the interlayer film is referred to as a ratio (tan ⁇ (1)/tan ⁇ (2)).
  • the ratio (tan ⁇ (1)/tan ⁇ (2)) is preferably 2.0 or more, and is preferably, 10.0 or less.
  • the ratio (tan ⁇ (1)/tan ⁇ (2)) is preferably 2.2 or more, more preferably 2.3 or more, still more preferably 2.4 or more, further preferably 2.5 or more, still further preferably 2.6 or more, yet still further preferably 2.7 or more, especially preferably 2.8 or more, especially more preferably 2.9 or more, and most preferably 3.0 or more.
  • the ratio (tan ⁇ (1)/tan ⁇ (2)) is preferably 9.0 or less, more preferably 8.0 or less, still more preferably 7.0 or less, further preferably 6.0 or less, and most preferably 5.0 or less.
  • the viscoelasticity measurement is specifically conducted in the following manner.
  • a test piece is stored in an environment at a room temperature of 23 ⁇ 2° C., and a humidity of 25 ⁇ 5% for 12 hours, and then the viscoelasticity is measured by using a dynamic viscoelasticity measuring device.
  • the measurement is conducted in the condition of raising the temperature from ⁇ 50° C. to 200° C. at a temperature rising speed of 3° C./min. in a shearing mode, and in the condition of a frequency of 1 Hz and a strain of 1%.
  • Examples of the dynamic viscoelasticity measuring device include a viscoelasticity analyzer “DVA-200” available from IT Keisoku Seigyo Co., Ltd., and the like.
  • the viscoelasticity measurement may be conducted using an interlayer film itself.
  • a peak of tan ⁇ derived from the layer containing a cured product, or a peak of tan ⁇ derived from the layer containing a resin may be read.
  • the interlayer film is a multilayer interlayer film having a two or more-layer structure
  • the layers may be delaminated to conduct the viscoelasticity measurement.
  • the lamination glass member and the interlayer film are delaminated, and the viscoelasticity measurement may be conducted using the delaminated interlayer film.
  • the thickness of the layer containing a cured product when the thickness of the layer containing a cured product is 0.3 mm or more and 2 mm or less, it is possible to easily measure the viscoelasticity by directly using the layer containing a cured product as a test piece.
  • the viscoelasticity may be measured using a test piece having a thickness of 0.3 mm or more and 2 mm or less by stacking a plurality of the layers containing a cured product, or separately preparing a layer containing a cured product in which only the thickness is adjusted.
  • the viscoelasticity may be measured using a test piece having a thickness of 0.3 mm or more and 2 mm or less by slicing or pressing the layer containing a cured product, or separately preparing a layer containing a cured product in which only the thickness is adjusted.
  • the viscoelasticity measurement for the layer containing a resin can be conducted in the same manner as the viscoelasticity measurement for the layer containing a cured product while the test piece is changed.
  • the storage modulus G′ at 100° C. of the layer containing a cured product can be measured in the viscoelasticity measurement for the layer containing a cured product.
  • the interlayer film according to the present invention may have a one-layer structure and may have a two or more-layer structure.
  • the interlayer film according to the present invention may have a two-layer structure and may have a three or more-layer structure.
  • the interlayer film according to the present invention may have a one-layer structure of only a first layer.
  • the first layer is the layer containing a cured product.
  • the interlayer film according to the present invention may include a first layer, and a second layer arranged on a first surface side of the first layer.
  • the first layer be the layer containing a cured product.
  • the interlayer film according to the present invention may include a first layer, and a second layer arranged on a first surface side of the first layer, and may further include a third layer arranged on a second surface side opposite to the first surface side of the first layer.
  • the first layer be the layer containing a cured product.
  • the layer containing a cured product be not a surface layer in the interlayer film, and it is preferred that the layer containing a cured product be an intermediate layer in the interlayer film. It is to be noted that the layer containing a cured product may be a surface layer in the interlayer film.
  • the visible light transmittance of the interlayer film is preferably 70% or more, more preferably 80% or more, further preferably 85% or more.
  • the visible light transmittance is measured at a wavelength ranging from 380 to 780 nm by using a spectrophotometer (“U-4100” available from Hitachi High-Tech Corporation) in conformity with JIS R3211:1998.
  • the visible light transmittance of the interlayer film may be measured while the interlayer film is arranged between two sheets of clear glass. It is preferred that the clear glass have a thickness of 2.0 mm.
  • FIG. 1 is a sectional view schematically showing an interlayer film for laminated glass in accordance with a first embodiment of the present invention.
  • An interlayer film 11 shown in FIG. 1 is a multi-layered interlayer film having a two or more-layer structure. Specifically, the interlayer film 11 has a three-layer structure. The interlayer film 11 is used for obtaining laminated glass. The interlayer film 11 is an interlayer film for laminated glass. The interlayer film 11 is provided with a first layer 1 , a second layer 2 and a third layer 3 . The second layer 2 is arranged on a first surface 1 a side of the first layer 1 to be layered thereon. The third layer 3 is arranged on a second surface 1 b side opposite to the first surface 1 a of the first layer 1 to be layered thereon. The first layer 1 is an intermediate layer.
  • Each of the second layer 2 and the third layer 3 is a protective layer and is a surface layer in the present embodiment.
  • the first layer 1 is arranged between the second layer 2 and the third layer 3 to be sandwiched therebetween.
  • the interlayer film 11 has a multilayer structure (second layer 2 /first layer 1 /third layer 3 ) in which the second layer 2 , the first layer 1 , and the third layer 3 are layered in this order.
  • the first layer 1 be the layer containing a cured product.
  • the second layer 2 may be the layer containing a cured product, or the third layer 3 may be the layer containing a cured product.
  • other layers may be arranged between the second layer 2 and the first layer 1 and between the first layer 1 and the third layer 3 , respectively. It is preferred that the second layer 2 and the first layer 1 , and the first layer 1 and the third layer 3 be directly layered. As the other layer, an adhesive layer can be recited.
  • FIG. 2 is a sectional view schematically showing an interlayer film for laminated glass in accordance with a second embodiment of the present invention.
  • An interlayer film 11 A shown in FIG. 2 is a single-layered interlayer film having a one-layer structure.
  • the interlayer film 11 A is a first layer.
  • the interlayer film 11 A is used for obtaining laminated glass.
  • the interlayer film 11 A is an interlayer film for laminated glass.
  • the interlayer film 11 A per se is the layer containing a cured product.
  • the details of the interlayer film according to the present invention the layer containing a cured product, the layer containing a resin, the first layer, the second layer and the third layer, and the details of each ingredient used in the interlayer film will be described.
  • the interlayer film includes the layer containing a cured product.
  • the curable compound for forming the cured product in the layer containing a cured product is a photocurable compound or a moisture-curable compound.
  • the curable compound is preferably a curable compound having a (meth)acryloyl group, and is more preferably a (meth)acrylic polymer.
  • the (meth)acrylic polymer be a polymer of a polymerizable composition containing a curable compound having a (meth)acryloyl group.
  • the polymerizable composition contains a polymerizable component.
  • the polymerizable composition may contain a photoreaction initiator.
  • the polymerizable composition may contain an auxiliary for accelerating the curing reaction together with the photoreaction initiator.
  • Representatives of the curable compound having a (meth)acryloyl group include (meth)acrylic ester. It is preferred that the (meth)acrylic polymer be a poly(meth)acrylic ester.
  • the polymerizable component include a (meth)acrylic ester having an alicyclic structure, a (meth)acrylic ester having a cyclic ether structure, a (meth)acrylic ester having an aromatic ring, a (meth)acrylic ester having a polar group, or an acyclic (meth)acrylic ester having 6 or less carbon atoms in the side chain.
  • a preferred (meth)acrylic ester it is possible to enhance both the sound insulating property and the ability to prevent foaming in good balance.
  • Examples of the (meth)acrylic ester having an alicyclic structure include isobornyl (meth)acrylate, cyclohexyl (meth)acrylate, dicyclopentanyl acrylate, and the like.
  • Examples of the (meth)acrylic ester having a cyclic ether structure include glycidyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate glycidyl ether, 3-hydroxypropyl (meth)acrylate glycidyl ether, 4-hydroxybutyl acrylate glycidyl ether, 5-hydroxypentyl (meth)acrylate glycidyl, 6-hydroxyhexyl (meth)acrylate glycidyl ether; (3-methyloxetan-3-yl)methyl (meth)acrylate, (3-propyloxetan-3-yl)methyl (meth)acrylate, (3-ethyloxetan-3-yl)methyl (meth)acrylate, (3-butyloxetan-3-yl)methyl (meth)acrylate, (3-ethyloxetan-3-yl)ethyl (meth) acrylate, (3-ethyloxetan-3-
  • Examples of the (meth)acrylic ester having an aromatic ring include benzyl acrylate, phenoxypolyethyleneglycol acrylate, and the like.
  • Examples of the (meth)acrylic ester having a polar group include (meth)acrylic esters having a hydroxyl group, an amide group, an amino group, an isocyanate group, a carboxyl group or the like as the polar group.
  • Examples of the (meth)acrylic ester having a hydroxyl group include 2-hydroxyethyl (meth)acrylate, hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxybutyl (meth)acrylate, and the like.
  • Examples of the (meth)acrylic ester having an amide group include N,N-dimethylaminopropyl (meth) acrylamide, N,N-dimethyl (meth)acrylamide, (meth)acryloyl morpholine, N-isopropyl (meth) acrylamide, N-hydroxyethyl (meth)acrylamide, and the like.
  • Examples of the (meth)acrylic ester having an amide group or an amino group include N-dialkylaminoalkyl (meth)acrylamide, N,N-dialkylaminoalkyl (meth)acrylamide, and the like.
  • Examples of the (meth)acrylic ester having an isocyanate group include triallylisocyanurate, derivatives thereof, and the like.
  • Examples of the (meth)acrylic ester having a carboxyl group include acrylic acid, ⁇ -carboxy-polycaprolactone monoacrylate, 2-acryloyloxyethylsuccinic acid, and the like.
  • the above-described (meth)acrylic ester may be a polycarboxylic ester having a (meth)acryloyl group.
  • examples of the polycarboxylic ester having a (meth)acryloyl group include 2-acryloyloxyethyl succinate, and the like.
  • a (meth)acrylic ester having a hydroxyl group is preferred, and 2-hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, or 4-hydroxybutyl (meth)acrylate is especially preferred.
  • Examples of the acyclic (meth)acrylic ester having 6 or less carbon atoms in the side chain include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, and the like.
  • the content of the acyclic (meth)acrylic ester having 8 or more carbon atoms in the side chain in 100% by weight of the polymerizable component be less than 20% by weight.
  • Examples of the (meth)acrylic ester include besides the compounds as recited above, diethyleneglycol monoethylether (meth) acrylate, 3-methoxybutyl (meth) acrylate, 2-acryloyloxyethyl-2-hydroxypropylphthalate, 2-acryloyloxyethyl-2-hydroxylpropylphthalate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, 1,6-hexane diol di(meth)acrylate, 1,9-nonane diol di(meth)acrylate, polytetramethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,3-butylene glycol di(meth)acrylate, 2,2-bis[4-(acryloxyethoxy)phenyl]propane di(meth)acrylate; trimethylolpropane
  • the above-described (meth)acrylic polymer may be a homopolymer of the above-described (meth)acrylic ester, or may be a copolymer of a polymerizable component containing the above-described (meth)acrylic ester.
  • photoreaction initiator examples include 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1,2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, bis( ⁇ 5-2,4-cyclopentadien-1-yl)-bis(2,6-difluoro-3-(1H-pyrrol-1-yl)-phenyl)titanium, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl
  • auxiliary examples include triethanol amine, triisopropanol amine, 4,4′-dimethylaminobenzophenone (Michler's ketone), 4,4′-diethylaminobenzophenone, 2-dimethylaminoethyl benzoate, ethyl 4-dimethylaminobenzoate, (n-butoxy)ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, and the like.
  • One kind of the auxiliary may be used alone and two or more kinds thereof may be used in combination.
  • auxiliary be benzyldimethylketal, 1-hydroxycyclohexylphenyl ketone, benzoylisopropyl ether, 4-(2-hydroxyethoxy)-phenyl(2-hydroxy-2-propyl) ketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, or triphenylmethylium tetrakis(pentafluorophenyl) borate.
  • the content of the photoreaction initiator is preferably 0.01% by weight or more, more preferably 0.1% by weight or more and is preferably 10% by weight or less, more preferably 5% by weight or less.
  • the photocurability and the storage stability further increase.
  • the content of the cured product is preferably 50% by weight or more, more preferably 60% by weight or more, further preferably 70% by weight or more, and especially preferably 80% by weight or more.
  • the content of the cured product in 100% by weight of the composition for forming the layer containing a cured product may be 100% by weight (total quantity).
  • the curable compound for forming the cured product in the layer containing a cured product is a photocurable compound such as a photocurable compound having a (meth)acryloyl group
  • a photocuring device such as an ultraviolet irradiation device be used to cure the photocurable compound.
  • the ultraviolet irradiation device include a box-type ultraviolet irradiation device, a belt-conveyer-type ultraviolet irradiation device, and the like.
  • Examples of the ultraviolet lamp installed in the ultraviolet irradiation device include a superhigh-pressure mercury lamp, a high-pressure mercury lamp, a low-pressure mercury lamp, a chemical lamp, a metal halide lamp, an excimer lamp, a UV-LED, and the like.
  • the ultraviolet lamp is preferably a chemical lamp or a UV-LED.
  • the ultraviolet dose (cumulative dose) is preferably 500 mJ or more, more preferably 1000 mJ or more, further preferably 1500 mJ or more, and especially preferably 2000 mJ or more.
  • the ultraviolet dose (cumulative dose) is preferably 20000 mJ or less, more preferably 10000 mJ or less, and further preferably 8000 mJ or less.
  • the irradiation intensity of the ultraviolet irradiation is preferably 0.1 mW or more, more preferably 0.5 mW or more, further preferably 1 mW or more, and especially preferably 2 mW or more.
  • the interlayer film include a layer containing a resin that is different from the cured product. It is preferred that the layer containing a resin that is different from the cured product (second resin layer) is a layer containing a resin that is different from a cured product of a photocurable compound, a cured product of a moisture-curable compound, and a curable compound of a curable compound having a (meth)acryloyl group.
  • the layer containing a resin that is different from the cured product is a resin layer that is different from the layer containing a cured product (first resin layer).
  • the interlayer film may not include the second resin layer.
  • Examples of the resin contained in the second resin layer include cured products of thermosetting compounds, thermoplastic resins, and the like.
  • the thermoplastic resin may be a thermoplastic elastomer.
  • the thermoplastic resin means a resin that softens and exhibits plasticity when it is heated, and hardens when it is cooled to room temperature.
  • the thermoplastic resins especially the thermoplastic elastomer means a resin that softens and exhibits plasticity when it is heated, and hardens to exhibits rubber elasticity when it is cooled to room temperature (25° C.)
  • thermoplastic resin examples include a polyvinyl acetal resin, a polyester resin, an aliphatic polyolefin, polystyrene, an ethylene-vinyl acetate copolymer resin, an ethylene-acrylic acid copolymer resin, a polyurethane resin, an ionomer resin, a polyvinyl alcohol resin, a polyvinyl acetate resin, and the like.
  • Thermoplastic resins other than these may be used.
  • thermoplastic resins exemplified above can be a thermoplastic elastomer by adjusting the molecular structure, the polymerization degree and the like of the resin.
  • the surface layer in the interlayer film contain a thermoplastic resin. It is preferred that each of the second layer and the third layer in the interlayer film having a second layer/first layer/third layer structure contain a thermoplastic resin.
  • thermoplastic resin be a polyvinyl acetal resin, an ionomer resin or an ethylene-vinyl acetate copolymer resin. From the viewpoint of further enhancing the impact resistance and cracking preventability of the laminated glass, it is more preferred that the thermoplastic resin be a polyvinyl acetal resin.
  • the polyvinyl acetal resin can be produced by acetalizing polyvinyl alcohol (PVA) with an aldehyde. It is preferred that the polyvinyl acetal resin be an acetalized product of polyvinyl alcohol.
  • the polyvinyl alcohol can be obtained by saponifying polyvinyl acetate. The saponification degree of the polyvinyl alcohol generally lies within the range of 70 to 99.9% by mole.
  • the average polymerization degree of the polyvinyl alcohol (PVA) is preferably 200 or more, more preferably 500 or more, still more preferably 1500 or more, further preferably 1600 or more, and is preferably 5000 or less, more preferably 4000 or less, further preferably 3500 or less, especially preferably 3000 or less.
  • PVA polyvinyl alcohol
  • the average polymerization degree of the polyvinyl alcohol is determined by a method in accordance with JIS K6726 “Testing methods for polyvinyl alcohol”.
  • the number of carbon atoms of the acetal group contained in the polyvinyl acetal resin is not particularly limited.
  • the aldehyde used at the time of producing the polyvinyl acetal resin is not particularly limited. It is preferred that the number of carbon atoms of the acetal group in the polyvinyl acetal resin fall within the range of 3 to 5 and it is more preferred that the number of carbon atoms of the acetal group be 3 or 4. When the number of carbon atoms of the acetal group in the polyvinyl acetal resin is 3 or more, the glass transition temperature of the interlayer film is sufficiently lowered.
  • the aldehyde is not particularly limited. In general, an aldehyde with 1 to 10 carbon atoms is preferably used. Examples of the aldehyde with 1 to 10 carbon atoms include formaldehyde, acetaldehyde, propionaldehyde, n-butyraldehyde, isobutyraldehyde, n-valeraldehyde, 2-ethylbutyraldehyde, n-hexylaldehyde, n-octylaldehyde, n-nonylaldehyde, n-decylaldehyde, formaldehyde, acetaldehyde, benzaldehyde, and the like.
  • Propionaldehyde, n-butyraldehyde, isobutyraldehyde, n-hexylaldehyde, or n-valeraldehyde is preferred, propionaldehyde, n-butyraldehyde, or isobutyraldehyde is more preferred, and n-butyraldehyde is further preferred.
  • One kind of the aldehyde may be used alone, and two or more kinds thereof may be used in combination.
  • the content of the hydroxyl group (the amount of hydroxyl groups) of the polyvinyl acetal resin is preferably 15% by mole or more, more preferably 18% by mole or more, and preferably 40% by mole or less, and more preferably 35% by mole or less.
  • the content of the hydroxyl group is the above lower limit or more, the adhesive force of the interlayer film is further enhanced.
  • the content of the hydroxyl group is the above upper limit or less, the flexibility of the interlayer film is enhanced and the handling of the interlayer film is facilitated.
  • the content of the hydroxyl group of the polyvinyl acetal resin is a mole fraction, represented in percentage, obtained by dividing the amount of ethylene groups to which the hydroxyl group is bonded by the total amount of ethylene groups in the main chain.
  • the amount of ethylene groups to which the hydroxyl group is bonded can be determined in conformity with JIS K6728 “Testing methods for polyvinyl butyral”.
  • the acetylation degree of the polyvinyl acetal resin is preferably 0.01% by mole or more, more preferably 0.5% by mole or more, and preferably 10% by mole or less, and more preferably 2% by mole or less.
  • the acetylation degree is the above lower limit or more, the compatibility between the polyvinyl acetal resin and a plasticizer is enhanced.
  • the acetylation degree is the above upper limit or less, with regard to the interlayer film and laminated glass, the moisture resistance thereof is enhanced.
  • the acetylation degree is a mole fraction, represented in percentage, obtained by dividing the amount of ethylene groups to which the acetyl group is bonded by the total amount of ethylene groups in the main chain.
  • the amount of ethylene groups to which the acetyl group is bonded can be determined in accordance with JIS K6728 “Testing methods for polyvinyl butyral”.
  • the acetalization degree of the polyvinyl acetal resin (the butyralization degree in the case of a polyvinyl butyral resin) is preferably 55% by mole or more, more preferably 60% by mole or more and is preferably 75% by mole or less, and more preferably 71% by mole or less.
  • the acetalization degree is the above lower limit or more, the compatibility between the polyvinyl acetal resin and a plasticizer is enhanced.
  • the acetalization degree is the above upper limit or less, the reaction time required for producing the polyvinyl acetal resin is shortened.
  • the acetalization degree is determined in the following manner. From the total amount of the ethylene group in the main chain, the amount of the ethylene group to which the hydroxyl group is bonded and the amount of the ethylene group to which the acetyl group is bonded are subtracted. The obtained value is divided by the total amount of the ethylene group in the main chain to obtain a mole fraction. The mole fraction represented in percentage is the acetalization degree.
  • the content of the hydroxyl group (the amount of hydroxyl groups), the acetalization degree (the butyralization degree) and the acetylation degree be calculated from the results determined by a method in accordance with JIS K6728 “Testing methods for polyvinyl butyral”.
  • a method in accordance with ASTM D1396-92 may be used.
  • the content of the hydroxyl group (the amount of hydroxyl groups), the acetalization degree (the butyralization degree) and the acetylation degree can be calculated from the results measured by a method in accordance with JIS K6728 “Testing methods for polyvinyl butyral”.
  • the interlayer film contain a tackifier resin. It is preferred that the layer containing a cured product (first resin layer) contain a tackifier resin. It is preferred that the layer containing a resin (second resin layer) contain a tackifier resin. It is preferred that the first layer contain a tackifier resin.
  • One kind of the tackifier resin may be used alone and two or more kinds thereof may be used in combination.
  • the tackifier resin examples include a styrene resin, a terpene resin, a rosin resin, and the like. From the viewpoint of enhancing the sound insulating property over a wide range of temperature while keeping haze satisfactorily, the tackifier resin is preferably a styrene resin. It is preferred that the styrene resin be an oligomer of styrene.
  • One exemplary commercially available product of the oligomer of styrene is “YS resin SX100” available from YASUHARA CHEMICAL CO., LTD.
  • the content of the tackifier resin per 100 parts by weight of the resin excluding the tackifier resin contained in the resin layer is preferably 10 parts by weight or more, more preferably 20 parts by weight or more, further preferably 30 parts by weight or more, and is preferably 150 parts by weight or less, more preferably 100 parts by weight or less.
  • the content of the tackifier resin is the above lower limit or more, it is possible to enhance the sound insulating property over a wide range of temperature while keeping haze satisfactorily.
  • the interlayer film contain a plasticizer. From the viewpoint of effectively enhancing the sound insulating property, it is preferred that the layer containing a cured product (first resin layer) contain a plasticizer. It is preferred that the layer containing a resin (second resin layer) contain a plasticizer. It is preferred that the first layer contain a plasticizer. It is preferred that the second layer contain a plasticizer. It is preferred that the third layer contain a plasticizer. By using the plasticizer, adhesive force between layers tends to be further increased. One kind of the plasticizer may be used alone and two or more kinds thereof may be used in combination.
  • plasticizer examples include paraffin oil, a benzoic ester plasticizer, an organic ester plasticizer, an organic phosphate plasticizer, and the like.
  • organic ester plasticizer examples include a monobasic organic acid ester, a polybasic organic acid ester, and the like.
  • phosphate plasticizer examples include an organic phosphate plasticizer, an organic phosphite plasticizer, and the like. It is preferred that the plasticizer be a liquid plasticizer.
  • paraffin oil examples include naphthenic process oil, white mineral oil, mineral oil, paraffin wax, liquid paraffin, and the like.
  • paraffin oil examples include “Diana process oil PW-90” available from Idemitsu Kosan Co., Ltd., “Diana process oil PW-100” available from Idemitsu Kosan Co., Ltd., “Diana process oil PW-32” available from Idemitsu Kosan Co., Ltd., and the like.
  • organic ester plasticizer examples include triethylene glycol di-2-ethylpropanoate, triethylene glycol di-2-ethylbutyrate, triethylene glycol di-2-ethylhexanoate, triethylene glycol dicaprylate, triethylene glycol di-n-octanoate, triethylene glycol di-n-heptanoate, tetraethylene glycol di-n-heptanoate, dibutyl sebacate, dioctyl azelate, dibutyl carbitol adipate, ethylene glycol di-2-ethylbutyrate, 1,3-propylene glycol di-2-ethylbutyrate, 1,4-butylene glycol di-2-ethylbutyrate, diethylene glycol di-2-ethylbutyrate, diethylene glycol di-2-ethylhexanoate, dipropylene glycol di-2-ethylbutyrate, triethylene glycol di-2-ethy
  • organic ester plasticizer examples include a diester plasticizer represented by the following structural formula (1).
  • R1 and R2 each represent an organic group with 2 to 10 carbon atoms
  • R3 represents an ethylene group, an isopropylene group or an n-propylene group
  • p represents an integer of 3 to 10. It is preferred that R1 and R2 in the foregoing formula (1) each be an organic group with 5 to 10 carbon atoms, and it is more preferred that R1 and R2 each be an organic group with 6 to 10 carbon atoms.
  • the plasticizer include triethylene glycol di-2-ethylhexanoate (3GO), triethylene glycol di-2-ethylbutyrate (3GH) or triethylene glycol di-2-ethylpropanoate. It is more preferred that the plasticizer include triethylene glycol di-2-ethylhexanoate or triethylene glycol di-2-ethylbutyrate, and it is further preferred that the plasticizer include triethylene glycol di-2-ethylhexanoate.
  • 3GO triethylene glycol di-2-ethylhexanoate
  • 3GH triethylene glycol di-2-ethylbutyrate
  • the plasticizer include triethylene glycol di-2-ethylhexanoate.
  • the content of the plasticizer per 100 parts by weight of the cured product is referred to as content (1).
  • the content (1) is preferably 5 parts by weight or more, more preferably 10 parts by weight or more, further preferably 20 parts by weight or more, and especially preferably 25 parts by weight or more, and is preferably 60 parts by weight or less, and more preferably 50 parts by weight or less.
  • the content (1) is the above lower limit or more, it is possible to effectively enhance the sound insulating property.
  • the content (1) is the above upper limit or less, the penetration resistance of laminated glass is further enhanced.
  • the content of the plasticizer per 100 parts by weight of the resin is referred to as content (2).
  • the content (2) is preferably 5 parts by weight or more, more preferably 10 parts by weight or more, further preferably 20 parts by weight or more, and is preferably 60 parts by weight or less, more preferably 55 parts by weight or less, further preferably 50 parts by weight or less.
  • the content (2) is the above lower limit or more, it is possible to effectively enhance the sound insulating property.
  • the content of the plasticizer is the above upper limit or less, the penetration resistance of laminated glass is further enhanced.
  • the interlayer film may contain a heat shielding substance.
  • the layer containing a cured product may contain a heat shielding substance.
  • the layer containing a resin may contain a heat shielding substance.
  • the first layer may contain a heat shielding substance.
  • the second layer may contain a heat shielding substance.
  • the third layer may contain a heat shielding substance.
  • One kind of the heat shielding substance may be used alone, and two or more kinds thereof may be used in combination.
  • the heat shielding substance may contain at least one kind of Ingredient X among a phthalocyanine compound, a naphthalocyanine compound, and an anthracyanine compound or contain heat shielding particles.
  • the heat shielding substance may contain both of the Ingredient X and the heat shielding particles.
  • the interlayer film may contain at least one kind of Ingredient X among a phthalocyanine compound, a naphthalocyanine compound and an anthracyanine compound.
  • the layer containing a cured product may contain the Ingredient X.
  • the layer containing a resin may contain the Ingredient X.
  • the first layer may contain the Ingredient X.
  • the second layer may contain the Ingredient X.
  • the third layer may contain the Ingredient X.
  • the Ingredient X is a heat shielding substance.
  • One kind of the Ingredient X may be used alone, and two or more kinds thereof may be used in combination.
  • the Ingredient X is not particularly limited.
  • As the Ingredient X conventionally known phthalocyanine compound, naphthalocyanine compound and anthracyanine compound can be used.
  • Examples of the Ingredient X include phthalocyanine, a derivative of phthalocyanine, naphthalocyanine, a derivative of naphthalocyanine, anthracyanine, a derivative of anthracyanine, and the like. It is preferred that each of the phthalocyanine compound and the derivative of phthalocyanine have a phthalocyanine skeleton. It is preferred that each of the naphthalocyanine compound and the derivative of naphthalocyanine have a naphthalocyanine skeleton. It is preferred that each of the anthracyanine compound and the derivative of anthracyanine have an anthracyanine skeleton.
  • the Ingredient X may contain a vanadium atom or a copper atom.
  • the Ingredient X may contain a vanadium atom, and may contain a copper atom.
  • the Ingredient X may be at least one kind of phthalocyanines containing a vanadium atom or a copper atom, and derivatives of phthalocyanine containing a vanadium atom or a copper atom.
  • the interlayer film may contain heat shielding particles.
  • the layer containing a cured product may contain heat shielding particles.
  • the layer containing a resin may contain heat shielding particles.
  • the first layer may contain heat shielding particles.
  • the second layer may contain heat shielding particles.
  • the third layer may contain heat shielding particles.
  • the heat shielding particle is of a heat shielding substance.
  • metal oxide particles may be used.
  • particles formed of an oxide of metal may be used.
  • infrared rays The energy amount of an infrared ray with a wavelength of 780 nm or longer which is longer than that of visible light is small as compared with an ultraviolet ray.
  • the thermal action of infrared rays is large, and when infrared rays are absorbed into a substance, heat is released from the substance. Accordingly, infrared rays are generally called heat rays.
  • the heat shielding particle means a particle capable of absorbing infrared rays.
  • heat shielding particles include metal oxide particles such as aluminum-doped tin oxide particles, indium-doped tin oxide particles, antimony-doped tin oxide particles (ATO particles), gallium-doped zinc oxide particles (GZO particles), indium-doped zinc oxide particles (IZO particles), aluminum-doped zinc oxide particles (AZO particles), niobium-doped titanium oxide particles, sodium-doped tungsten oxide particles, cesium-doped tungsten oxide particles, thallium-doped tungsten oxide particles, rubidium-doped tungsten oxide particles, tin-doped indium oxide particles (ITO particles), tin-doped zinc oxide particles and silicon-doped zinc oxide particles, lanthanum hexaboride (LaB 6 ) particles, and the like. Heat shielding particles other than these may be used.
  • the interlayer film may contain at least one kind of metal salt (hereinafter, also referred to as Metal salt M) among an alkali metal salt, an alkaline earth metal salt, and a magnesium salt.
  • the layer containing a cured product may contain the Metal salt M.
  • the layer containing a resin may contain the Metal salt M.
  • the first layer may contain the Metal salt M.
  • the second layer may contain the metal salt M.
  • the third layer may contain the Metal salt M.
  • the Metal salt M may contain at least one kind of metal selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr and Ba.
  • an alkali metal salt of an organic acid having 2 to 16 carbon atoms an alkali earth metal salt of an organic acid having 2 to 16 carbon atoms, or a magnesium salt of an organic acid having 2 to 16 carbon atoms can be used.
  • magnesium carboxylate with 2 to 16 carbon atoms and the potassium carboxylate with 2 to 16 carbon atoms include magnesium acetate, potassium acetate, magnesium propionate, potassium propionate, magnesium 2-ethylbutyrate, potassium 2-ethylbutanoate, magnesium 2-ethylhexanoate, potassium 2-ethylhexanoate, and the like.
  • the interlayer film may contain an ultraviolet ray screening agent.
  • the layer containing a cured product may contain an ultraviolet ray screening agent.
  • the layer containing a resin may contain an ultraviolet ray screening agent.
  • the first layer may contain an ultraviolet ray screening agent.
  • the second layer may contain an ultraviolet ray screening agent.
  • the third layer may contain an ultraviolet ray screening agent.
  • Examples of the ultraviolet ray screening agent include an ultraviolet ray absorber. It is preferred that the ultraviolet ray screening agent be an ultraviolet ray absorber.
  • Examples of the ultraviolet ray screening agent include an ultraviolet ray screening agent containing a metal atom, an ultraviolet ray screening agent containing a metal oxide, an ultraviolet ray screening agent having a benzotriazole structure (a benzotriazole compound), an ultraviolet ray screening agent having a benzophenone structure (a benzophenone compound), an ultraviolet ray screening agent having a triazine structure (a triazine compound), an ultraviolet ray screening agent having a malonic acid ester structure (a malonic acid ester compound), an ultraviolet ray screening agent having an oxanilide structure (an oxanilide compound), an ultraviolet ray screening agent having a benzoate structure (a benzoate compound), and the like.
  • Examples of the ultraviolet ray screening agent containing a metal atom include platinum particles, particles in which the surface of platinum particles is coated with silica, palladium particles, particles in which the surface of palladium particles is coated with silica, and the like. It is preferred that the ultraviolet ray screening agent not be heat shielding particles.
  • Examples of the ultraviolet ray screening agent containing a metal oxide include zinc oxide, titanium oxide, cerium oxide, and the like. Furthermore, with regard to the ultraviolet ray screening agent containing a metal oxide, the surface thereof may be coated with any material. Examples of the coating material for the surface of the ultraviolet ray screening agent containing a metal oxide include an insulating metal oxide, a hydrolyzable organosilicon compound, a silicone compound, and the like.
  • the insulating metal oxide examples include silica, alumina, zirconia, and the like.
  • the insulating metal oxide has a band-gap energy of 5.0 eV or more.
  • Examples of the ultraviolet ray screening agent having a benzotriazole structure include 2-(2′-hydroxy-5′-methylphenyl)benzotriazole (“Tinuvin P” available from BASF Japan Ltd.), 2-(2′-hydroxy-3′,5′-di-t-butylphenyl)benzotriazole (“Tinuvin 320” available from BASF Japan Ltd.), 2-(2′-hydroxy-3′-t-butyl-5-methylphenyl)-5-chlorobenzotriazole (“Tinuvin 326” available from BASF Japan Ltd.), 2-(2′-hydroxy-3′,5′-di-amylphenyl)benzotriazole (“Tinuvin 328” available from BASF Japan Ltd.), and the like.
  • Examples of the ultraviolet ray screening agent having a benzophenone structure include octabenzone (“Chimassorb 81” available from BASF Japan Ltd.), and the like.
  • Examples of the ultraviolet ray screening agent having a triazine structure include “LA-F70” available from ADEKA CORPORATION, 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-[(hexyl)oxy]-phenol (“Tinuvin 1577FF” available from BASF Japan Ltd.), and the like.
  • Examples of the ultraviolet ray screening agent having a malonic acid ester structure include dimethyl 2-(p-methoxybenzylidene)malonate, tetraethyl-2,2-(1,4-phenylenedimethylidene)bismalonate, 2-(p-methoxybenzylidene)-bis(1,2,2,6,6-pentamethyl-4-piperidinyl)malonate, and the like.
  • Examples of a commercial product of the ultraviolet ray screening agent having a malonic acid ester structure include Hostavin B-CAP, Hostavin PR-25 and Hostavin PR-31 (any of these is available from Clariant Japan K.K.).
  • Examples of the ultraviolet ray screening agent having an oxanilide structure include a kind of oxalic acid diamide having a substituted aryl group and the like on the nitrogen atom such as N-(2-ethylphenyl)-N′-(2-ethoxy-5-t-butylphenyl)oxalic acid diamide, N-(2-ethylphenyl)-N′-(2-ethoxy-phenyl)oxalic acid diamide and 2-ethyl-2′-ethoxy-oxanilide (“Sanduvor VSU” available from Clariant Japan K.K.).
  • Examples of the ultraviolet ray screening agent having a benzoate structure include 2,4-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate (“Tinuvin 120” available from BASF Japan Ltd.), and the like.
  • the interlayer film may contain an oxidation inhibitor.
  • the layer containing a cured product may contain an oxidation inhibitor.
  • the layer containing a resin may contain an oxidation inhibitor.
  • the first layer may contain an oxidation inhibitor.
  • the second layer may contain an oxidation inhibitor.
  • the third layer may contain an oxidation inhibitor.
  • One kind of the oxidation inhibitor may be used alone, and two or more kinds thereof may be used in combination.
  • the oxidation inhibitor examples include a phenol-based oxidation inhibitor, a sulfur-based oxidation inhibitor, a phosphorus-based oxidation inhibitor, and the like.
  • the phenol-based oxidation inhibitor is an oxidation inhibitor having a phenol skeleton.
  • the sulfur-based oxidation inhibitor is an oxidation inhibitor containing a sulfur atom.
  • the phosphorus-based oxidation inhibitor is an oxidation inhibitor containing a phosphorus atom.
  • phenol-based oxidation inhibitor examples include 2,6-di-t-butyl-p-cresol (BHT), butyl hydroxyanisole (BHA), 2,6-di-t-butyl-4-ethylphenol, stearyl ⁇ -(3,5-di-t-butyl-4-hydroxyphenyl)propionate, 2,2′-methylenebis-(4-methyl-6-butylphenol), 2,2′-methylenebis-(4-ethyl-6-t-butylphenol), 4,4′-butylidene-bis-(3-methyl-6-t-butylphenol), 1,1,3-tris-(2-methyl-hydroxy-5-t-butylphenyl)butane, tetrakis[methylene-3-(3′,5′-butyl-4-hydroxyphenyl)propionate]methane, 1,3,3-tris-(2-methyl-4-hydroxy-5-t-butylphenol)butane, 1,3,5-trimethyl
  • Examples of the phosphorus-based oxidation inhibitor include tridecyl phosphite, tris(tridecyl) phosphite, triphenyl phosphite, trinonylphenyl phosphite, bis(tridecyl)pentaerithritol diphosphite, bis(decyl)pentaerithritol diphosphite, tris(2,4-di-t-butylphenyl) phosphite, bis(2,4-di-t-butyl-6-methylphenyl)ethyl ester phosphorous acid, 2,2′-methylenebis(4,6-di-t-butyl-1-phenyloxy)(2-ethylhexyloxy)phosphorus, and the like.
  • One kind or two or more kinds among these oxidation inhibitors are preferably used.
  • Examples of a commercial product of the oxidation inhibitor include “IRGANOX 245” available from BASF Japan Ltd., “IRGAFOS 168” available from BASF Japan Ltd., “IRGAFOS 38” available from BASF Japan Ltd., “Sumilizer BHT” available from Sumitomo Chemical Co., Ltd., “H-BHT” available from Sakai Chemical Industry Co., Ltd., “IRGANOX 1010” available from BASF Japan Ltd., and the like.
  • Each of the interlayer film, the layer containing a cured product, the layer containing a resin, the first layer, the second layer, and the third layer may contain additives such as a coupling agent, a dispersing agent, a surfactant, a flame retardant, an antistatic agent, a pigment, a dye, an adhesive force regulator other than metal salt, a moisture-resistance agent, a fluorescent brightening agent, and an infrared ray absorber, as necessary.
  • additives such as a coupling agent, a dispersing agent, a surfactant, a flame retardant, an antistatic agent, a pigment, a dye, an adhesive force regulator other than metal salt, a moisture-resistance agent, a fluorescent brightening agent, and an infrared ray absorber, as necessary.
  • additives such as a coupling agent, a dispersing agent, a surfactant, a flame retardant, an antistatic agent, a pigment, a dye, an adhesive force
  • the thickness of the interlayer film is not particularly limited. From the viewpoint of the practical aspect and the viewpoint of sufficiently enhancing the penetration resistance and the flexural rigidity of laminated glass, the thickness of the interlayer film is preferably 0.1 mm or more, more preferably 0.25 mm or more, and is preferably 3 mm or less, more preferably 1.5 mm or less. When the thickness of the interlayer film is the above lower limit or more, the penetration resistance and the flexural rigidity of laminated glass are further enhanced. When the thickness of the interlayer film is the above upper limit or less, the transparency of the interlayer film is further improved.
  • the thickness of the interlayer film is designated as T.
  • the thickness of the layer containing a cured product is preferably 0.03T or more, more preferably 0.06T or more, and further preferably 0.1T or more, and is preferably 1T or less, more preferably 0.5T or less, and further preferably 0.2T or less.
  • the thickness of the layer containing a resin is preferably 0.3T or more, more preferably 0.35T or more, and further preferably 0.4T or more, and is preferably 0.95T or less, and more preferably 0.9T or less.
  • the thickness of the layer containing a cured product is preferably 15 ⁇ m or more, more preferably 40 ⁇ m or more, and further preferably 80 ⁇ m or more, and is preferably 600 ⁇ m or less, more preferably 300 ⁇ m or less, and further preferably 150 ⁇ m or less.
  • the thickness of the layer containing a resin is preferably 200 ⁇ m or more, more preferably 400 ⁇ m or more, and further preferably 600 ⁇ m or more, and is preferably 1200 ⁇ m or less, more preferably 1000 ⁇ m or less, and further preferably 850 ⁇ m or less.
  • the interlayer film may be an interlayer film having a uniform thickness, or may be an interlayer film having varying thickness.
  • the sectional shape of the interlayer film may be a rectangular shape and may be a wedge-like shape.
  • the production method of the interlayer film according to the present invention is not particularly limited.
  • examples of the production method of the interlayer film according to the present invention include a method of extruding a resin composition with an extruder.
  • examples of the production method of the interlayer film according to the present invention include a method of separately forming resin compositions used for constituting respective layers into respective layers, and then, for example, layering the obtained layers, a method of coextruding resin compositions used for constituting respective layers with an extruder and layering the layers, and the like.
  • a production method of extrusion-molding is preferred because the method is suitable for continuous production.
  • the second layer and the third layer contain the same polyvinyl acetal resin, and it is more preferred that the second layer and the third layer contain the same polyvinyl acetal resin and the same plasticizer.
  • the second layer and the third layer be formed of the same resin composition.
  • the interlayer film have protrusions and recesses on at least one surface of the surfaces of both sides. It is more preferred that the interlayer film have protrusions and recesses on surfaces of both sides.
  • Examples of the method for forming the protrusions and recesses include, but are not particularly limited to, a lip emboss method, an emboss roll method, a calender roll method, a profile extrusion method, and the like.
  • the emboss roll method is preferred because a large number of embosses of the protrusions and recesses, which is a quantitatively constant protrusion and recess pattern, can be formed.
  • the laminated glass according to the present invention includes a first lamination glass member, a second lamination glass member and the aforementioned interlayer film for laminated glass.
  • the above-mentioned interlayer film for laminated glass is arranged between the first lamination glass member and the second lamination glass member.
  • FIG. 3 is a sectional view schematically showing an example of laminated glass prepared with the interlayer film for laminated glass shown in FIG. 1 .
  • the laminated glass 31 shown in FIG. 3 is provided with a first lamination glass member 21 , a second lamination glass member 22 and an interlayer film 11 .
  • the interlayer film 11 is arranged between the first lamination glass member 21 and the second lamination glass member 22 to be sandwiched therebetween.
  • the first lamination glass member 21 is layered on a first surface 11 a of the interlayer film 11 .
  • the second lamination glass member 22 is layered on a second surface 11 b opposite to the first surface 11 a of the interlayer film 11 .
  • the first lamination glass member 21 is layered on an outer surface 2 a of the second layer 2 .
  • the second lamination glass member 22 is layered on an outer surface 3 a of a third layer 3 .
  • FIG. 4 is a sectional view schematically showing an example of laminated glass prepared with the interlayer film for laminated glass shown in FIG. 2 .
  • the laminated glass 31 A shown in FIG. 4 is provided with a first lamination glass member 21 , a second lamination glass member 22 and an interlayer film 11 A.
  • the interlayer film 11 A is arranged between the first lamination glass member 21 and the second lamination glass member 22 to be sandwiched therebetween.
  • the first lamination glass member 21 is layered on a first surface 11 a of the interlayer film 11 A.
  • the second lamination glass member 22 is layered on a second surface 11 b opposite to the first surface 11 a of the interlayer film 11 A.
  • the laminated glass according to the present invention includes a first lamination glass member, a second lamination glass member, and an interlayer film, and the interlayer film is the interlayer film for laminated glass according to the present invention.
  • the above-mentioned interlayer film is arranged between the first lamination glass member and the second lamination glass member.
  • first lamination glass member be the first glass plate. It is preferred that the second lamination glass member be the second glass plate.
  • first and second lamination glass members examples include a glass plate, a PET (polyethylene terephthalate) film, and the like.
  • laminated glass laminated glass in which an interlayer film is sandwiched between a glass plate and a PET film or the like, as well as laminated glass in which an interlayer film is sandwiched between two glass plates, is included.
  • the laminated glass is a laminate provided with a glass plate, and it is preferred that at least one glass plate be used. It is preferred that each of the first lamination glass member and the second lamination glass member be a glass plate or a PET film, and the laminated glass be provided with a glass plate as at least one among the first lamination glass member and the second lamination glass member. It is especially preferred that both of the first and second lamination glass members be glass plates.
  • the glass plate examples include a sheet of inorganic glass and a sheet of organic glass.
  • the inorganic glass examples include float plate glass, heat ray-absorbing plate glass, heat ray-reflecting plate glass, polished plate glass, figured glass, wired plate glass, and the like.
  • the organic glass is synthetic resin glass substituted for inorganic glass.
  • the organic glass examples include a polycarbonate plate, a poly(meth)acrylic resin plate, and the like.
  • the poly(meth)acrylic resin plate examples include a polymethyl (meth)acrylate plate, and the like.
  • each of the first lamination glass member and the second lamination glass member is preferably 1 mm or more, and is preferably 5 mm or less, and more preferably 3 mm or less.
  • the thickness of the glass plate is preferably 0.5 mm or more, more preferably 0.7 mm or more, preferably 5 mm or less and more preferably 3 mm or less.
  • the thickness of the PET film is preferably 0.03 mm or more and is preferably 0.5 mm or less.
  • the method for producing the laminated glass is not particularly limited.
  • the interlayer film is sandwiched between the first lamination glass member and the second lamination glass member, and then, passed through pressure rolls or subjected to decompression suction in a rubber bag, so that the air remaining between the first and the second lamination glass members and the interlayer film is removed.
  • the members are preliminarily bonded together at about 70 to 110° C. to obtain a laminate.
  • the members are press-bonded together at about 120 to 150° C. and under a pressure of 1 to 1.5 MPa. In this way, laminated glass can be obtained.
  • layers in the interlayer film may be layered.
  • each of the interlayer film and the laminated glass can be used for automobiles, railway vehicles, aircraft, ships, buildings and the like. Each of the interlayer film and the laminated glass can also be used for applications other than these applications. It is preferred that the interlayer film and the laminated glass be an interlayer film and laminated glass for vehicles or for buildings respectively, and it is more preferred that the interlayer film and the laminated glass be an interlayer film and laminated glass for vehicles respectively. Each of the interlayer film and the laminated glass can be used for a windshield, side glass, rear glass or roof glass of an automobile, and the like. The interlayer film and the laminated glass are suitably used for automobiles. The interlayer film is used for obtaining laminated glass of an automobile.
  • the acetalization degree (the butyralization degree), the acetylation degree and the content of the hydroxyl group were measured by a method in accordance with JIS K6728 “Testing methods for polyvinyl butyral”.
  • JIS K6728 “Testing methods for polyvinyl butyral”.
  • the acetalization degree is calculated by measuring the acetylation degree and the content of the hydroxyl group, and calculating a mole fraction from the obtained measurement results, and then subtracting the acetylation degree and the content of hydroxyl groups from 100% by mole.
  • Polyvinyl acetal resin (1) (using n-butyl aldehyde, polymerization degree: 1700, content of hydroxyl group: 33.5% by mole, acetylation degree: 1% by mole, butyralization degree: 65.5% by mole)
  • Polyvinyl acetal resin (2) (using n-butyl aldehyde, polymerization degree: 3000, content of hydroxyl group: 24% by mole, acetylation degree: 12% by mole, butyralization degree: 64% by mole)
  • a polymerizable composition having the blending composition shown in the following Tables 1 and 2 was sandwiched between two PET sheets having subjected to a mold release treatment on one side (available from Nippa Corporation, having a thickness of 50 ⁇ m) to form a polymerizable composition layer having a thickness of 100 ⁇ m.
  • a spacer was arranged around the two PET sheets.
  • the polymerizable composition layer was irradiated with ultraviolet rays at a dose of 3000 mJ/cm 2 with a high pressure mercury UV lamp to cure the polymerizable composition by reaction, and thus (meth)acrylic polymers (1) to (9), (11), (12), (A) and (B) were obtained.
  • a polymerizable composition having the blending composition shown in the following Table 2 was sandwiched between two PET sheets having subjected to a mold release treatment on one side (available from Nippa Corporation, having a thickness of 50 ⁇ m) to form a polymerizable composition layer having a thickness of 810 ⁇ m.
  • a spacer was arranged around the two PET sheets.
  • the polymerizable composition layer was irradiated with ultraviolet rays at a dose of 5000 mJ/cm 2 with a chemical lamp (“FL20SBL” available from TOSHIBA CORPORATION) to cure the polymerizable composition by reaction. Further, by heating at 100° C. for 30 minutes after peeling off one of the PET sheets, the (meth)acrylic polymer (10) was obtained.
  • Tinuvin 326 (2-(2′-hydroxy-3′-t-butyl-5-methylphenyl)-5-chlorobenzotriazole, “Tinuvin 326” available from BASF Japan Ltd.)
  • Additive (2) YS resin SX100 (styrene oligomer, available from YASUHARA CHEMICAL CO., LTD.)
  • the (meth)acrylic polymer (1) obtained in the above (layer containing a cured product, having a thickness of 100 ⁇ m) was prepared.
  • the following ingredients were mixed, and kneaded sufficiently with a mixing roll to obtain a composition for forming a second layer and a third layer.
  • Metal salt M (Mg mixture) in such an amount that is 70 ppm in the obtained second layer and third layer
  • Ultraviolet ray screening agent Tinuvin 3266 in an amount of 0.2% by weight in the obtained second layer and third layer
  • composition for forming the second layer and the third layer was extruded with an extruder to obtain a second layer and the third layer (each having a thickness of 380 ⁇ m).
  • a mold-release-treated PET sheet laminated on the first layer was peeled off, and the first layer and the second layer were bonded together by means of a roll laminator, and press-bonded to give a two-layer laminate. Subsequently, another mold-release-treated PET sheet laminated on the first layer was peeled off, and the first layer and the third layer were press-bonded in the same manner to obtain an interlayer film having a structure of second layer/first layer/third layer.
  • the obtained interlayer film was cut into a size of 25 mm wide and 300 mm long.
  • two glass plates (clear float glass, 25 mm wide, 300 mm long and 2 mm thick) were prepared.
  • the interlayer film was sandwiched between the two glass plates to obtain a laminate.
  • the laminate was put into a rubber bag and the inside thereof was degassed for 20 minutes with a degree of vacuum of 2.6 kPa, after which the laminate in the degassed condition was transferred into an oven, and vacuum-pressed by retention at 90° C. for 30 minutes, and thus the laminate was preliminarily press-bonded.
  • the preliminarily press-bonded laminate was subjected to press-bonding for 20 minutes under conditions of 135° C. and a pressure of 1.2 MPa in an autoclave to obtain a sheet of laminated glass.
  • the obtained interlayer film was cut into a size of 100 mm wide and 100 mm long.
  • two glass plates (clear float glass, 100 mm wide, 100 mm long and 2 mm thick) were prepared.
  • the interlayer film was sandwiched between the two glass plates to obtain a laminate.
  • the laminate was put into a rubber bag and the inside thereof was degassed for 20 minutes with a degree of vacuum of 2.6 kPa, after which the laminate in the degassed condition was transferred into an oven, and vacuum-pressed by retention at 90° C. for 30 minutes, and thus the laminate was preliminarily press-bonded.
  • the preliminarily press-bonded laminate was subjected to press-bonding for 20 minutes under conditions of 135° C. and a pressure of 1.2 MPa in an autoclave to obtain a sheet of laminated glass.
  • An interlayer film was obtained in the same manner as that in Example 1 except that the kinds and the amounts of the ingredients were set to those shown in the following Tables 3 and 4.
  • Metal salt M, an ultraviolet ray screening agent, and an oxidation inhibitor were blended in the same kinds and amounts as those in Example 1 (omitted in Tables 3 and 4).
  • Laminated glass was obtained in the same manner as that in Example 1 except that the obtained interlayer film was used.
  • the (meth)acrylic polymer (10) obtained in the above (layer containing a cured product, having a thickness of 810 ⁇ m) was prepared.
  • Laminated glass was obtained in the same manner as that in Example 1 except that the obtained interlayer film was used.
  • Preparation of first layer The ingredients shown in Table 4 were mixed, and kneaded sufficiently with a mixing roll to obtain a composition for forming a first layer, and then the composition was press-molded to have a thickness of 100 ⁇ m to obtain a layer containing a cured product of a (meth)acrylic polymer (11) or a cured product of a (meth)acrylic polymer (12).
  • An interlayer film was obtained in the same manner as that in Example 1 except that the kinds and the amounts of the ingredients were set to those shown in the following Table 4.
  • Metal salt M, an ultraviolet ray screening agent, and an oxidation inhibitor were blended in the same kinds and amounts as that in Example 1 (omitted in Table 4).
  • Laminated glass was obtained in the same manner as that in Example 1 except that the obtained interlayer film was used.
  • One hundred parts by weight of a polyvinyl acetal resin (2), 75 parts by weight of a plasticizer (3GO), an ultraviolet ray screening agent (Tinuvin 326) in such an amount that is to be 0.2% by weight in the obtained interlayer film, and an oxidation inhibitor (BHT) in such an amount that is to be 0.2% by weight in the obtained interlayer film were mixed sufficiently with a mixing roll to obtain a composition for forming a first layer.
  • a plasticizer 3GO
  • an ultraviolet ray screening agent Tinuvin 326
  • BHT oxidation inhibitor
  • Example 1 A composition for forming a second layer and a third layer the same as that in Example 1 was prepared.
  • an interlayer film having a structure of the second layer/the first layer/the third layer (thickness of first layer: 100 ⁇ m, the second layer and the third layer each having a thickness of 380 ⁇ m) was obtained.
  • Laminated glass was obtained in the same manner as that in Example 1 except that the obtained interlayer film was used.
  • An interlayer film was prepared in the same manner as that in Comparative Example 1 except that the kinds and the amounts of the ingredients were set to those shown in the following Table 5, and the thickness was set as shown in the following Table 5.
  • Metal salt M, an ultraviolet ray screening agent, and an oxidation inhibitor were blended in the same kinds and amounts as those in Comparative Example 1 (omitted in Table 5).
  • Laminated glass was obtained in the same manner as that in Example 1 except that the obtained interlayer film was used.
  • the following ingredients were mixed, and kneaded sufficiently with a mixing roll to obtain a composition for forming an interlayer film.
  • Additive (1) 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene 75 parts by weight
  • composition for forming an interlayer film was extruded with an extruder to obtain an interlayer film (810 ⁇ m thick).
  • Laminated glass was obtained in the same manner as that in Example 1 except that the obtained interlayer film was used.
  • Acrylic (PMMA) polymer was prepared as a composition for forming a first layer.
  • Example 1 A composition for forming a second layer and a third layer the same as that in Example 1 was prepared.
  • an interlayer film having a structure of the second layer/the first layer/the third layer (thickness of first layer: 100 ⁇ m, the second layer and the third layer each having a thickness of 380 ⁇ m) was obtained.
  • Laminated glass was obtained in the same manner as that in Example 1 except that the obtained interlayer film was used.
  • An interlayer film was obtained in the same manner as that in Example 1 except that the kinds and the amounts of the ingredients were set to those shown in the following Table 5.
  • Metal salt M, an ultraviolet ray screening agent, and an oxidation inhibitor were blended in the same kinds and amounts as those in Example 1 (omitted in Table 5).
  • Laminated glass was obtained in the same manner as that in Example 1 except that the obtained interlayer film was used.
  • dynamic viscoelasticity measurement was conducted.
  • the following items were evaluated by measuring dynamic viscoelasticity in the condition of raising the temperature from ⁇ 50° C. to 200° C. at a temperature rising speed of 3° C./min. in a shearing mode, and in the condition of a frequency of 1 Hz and a strain of 1%, using a dynamic viscoelasticity analyzer (DVA-200 available from IT Keisoku Seigyo Co. Ltd.).
  • the obtained laminated glass was excited with a vibration generator for damping test (“Vibrator G21-005D” available from Shinken. Co., Ltd.).
  • the resultant vibration characteristic was amplified with a mechanical impedance measuring device (“XG-81” available from RION Co., Ltd.), and the vibration spectrum was analyzed with an FFT spectrum analyzer (“FFT analyzer SA-01A2” available from RION Co., Ltd.).
  • ⁇ primary loss factor
  • ⁇ primary loss factor is 0.2 or more and less than 0.35
  • ⁇ primary loss factor is 0.1 or more and less than 0.2
  • Haze of a laminated glass directly after preparation was measured. After storing the laminated glass directly after preparation, at 23° C. and 50% RH for 4 weeks, the haze of the laminated glass after storage was measured.
  • ⁇ ratio of haze after storage to haze before storage is 0.99 or more and 1.01 or less
  • ratio of haze after storage to haze before storage is 0.5 or more and less than 0.99, or more than 1.01 and 1.5 or less
  • ratio of haze after storage to haze before storage is less than 0.5 or more than 1.5
  • EA ethyl acrylate (available from NIPPON SHOKUBAI CO., LTD.)
  • HEA 2-hydroxyethyl acrylate (available from OSAKA ORGANIC CHEMICAL INDUSTRY LTD.)
  • BzA benzyl acrylate (available from OSAKA ORGANIC CHEMICAL INDUSTRY LTD., VISCOAT #160)
  • n-butyl acrylate available from NIPPON SHOKUBAI CO., LTD.
  • THF-A tetrahydrofurfuryl acrylate (available from OSAKA ORGANIC CHEMICAL INDUSTRY LTD., VISCOAT #150)
  • CHA cyclohexyl acrylate (available from OSAKA ORGANIC CHEMICAL INDUSTRY LTD., VISCOAT #155)
  • HPA hydroxypropyl acrylate (available from OSAKA ORGANIC CHEMICAL INDUSTRY LTD.)
  • CTFA (#200): cyclic trimethylolpropane formal acrylate (available from OSAKA ORGANIC CHEMICAL INDUSTRY LTD., VISCOAT #200)
  • 2-EHA 2-ethylhexyl acrylate (available from NIPPON SHOKUBAI CO., LTD.)
  • ISTA isostearyl acrylate (available from OSAKA ORGANIC CHEMICAL INDUSTRY LTD.)
  • 4HBA 4-hydroxybutyl acrylate (available from OSAKA ORGANIC CHEMICAL INDUSTRY LTD.)
  • IBOA isobornyl acrylate (available from NIPPON SHOKUBAI CO., LTD.)
  • IRGACURE 184 2,2-dimethoxy-1,2-diphenylethan-1-one (available from BASF)

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US11731399B2 (en) 2019-07-02 2023-08-22 Sekisui Chemical Co. Ltd. Interlayer film for laminated glass, and laminated glass

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